Sodium Hydroxide → HCID 15165714, compound

HRID 1493140Notes

Reaction equation

HRID 1493140 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=[C:22]2[C:28]3[CH:29]=[C:30]([CH2:33][NH2:34])[CH:31]=[CH:32][C:27]=3[CH:26]=[CH:25][C:24]3[CH:35]=[CH:36][CH:37]=[CH:38][C:23]2=3)[CH2:18][CH2:17]1.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([O:52][CH3:53])[C:49]=1[O:50][CH3:51])[C:44](Cl)=[O:45].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:53][O:52][C:48]1[CH:47]=[C:43]([CH:42]=[C:41]([O:40][CH3:39])[C:49]=1[O:50][CH3:51])[C:44]([NH:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]2[CH:26]=[CH:25][C:24]3[CH:35]=[CH:36][CH:37]=[CH:38][C:23]=3[C:22](=[C:19]3[CH2:18][CH2:17][N:16]([CH3:15])[CH2:21][CH2:20]3)[C:28]=2[CH:29]=1)=[O:45]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 15165713HCID 15165713, compound

Product 1

HCID 15165714HCID 15165714, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 0.50 g (1.26 mmol) of the dihydrochloride salt of 1-methyl-4-(3-aminomethyl-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine and 0.25 g (1.08 mmol) 3,4,5-trimethoxybenzoyl chloride in 25 ml of toluene was added 1 ml of 10% aqueous sodium hydroxide. The mixture was shaken vigorously for 5 minutes. The toluene was removed by evaporation under reduced pressure and the residual gum was redissolved in chloroform. This chloroform phase was separated, dried over magnesium sulfate, filtered, and the chloroform was removed by evaporation. The crystalline residue was recrystallized from acetonitrile to give 3,4,5-trimethoxy-N-((5-(1-methyl-4-piperidinylidene)-5H-dibenzo[a,d]cyclohepten-3-yl)methyl)benzamide, mp 200°-202° C.

Workup

  1. customThe toluene was removed by evaporation under reduced pressure
  2. dissolutionthe residual gum was redissolved in chloroform
  3. customThis chloroform phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe chloroform was removed by evaporation
  7. customThe crystalline residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-35c4a79d5a2e482eb6c7732382327646
Source dataset
uspto-grants-1991_06
Patent number
US05021426

Reaction notes

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